# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_cd212367 _database_code_depnum_ccdc_archive 'CCDC 907194' #TrackingRef 'cd212367.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H16 O2' _chemical_formula_weight 300.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 17.1797(15) _cell_length_b 6.1625(5) _cell_length_c 14.8950(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1576.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2235 _cell_measurement_theta_min 4.742 _cell_measurement_theta_max 44.882 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.254 _exptl_crystal_size_mid 0.212 _exptl_crystal_size_min 0.116 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.59683 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8941 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2810 _reflns_number_gt 2307 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0714P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.4(13) _chemical_absolute_configuration ad _refine_ls_number_reflns 2810 _refine_ls_number_parameters 208 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.1082 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.40458(9) 0.35736(19) 0.68162(9) 0.0539(4) Uani 1 1 d . . . O2 O 0.52406(7) 0.35544(19) 0.75160(11) 0.0578(4) Uani 1 1 d . . . C1 C 0.39968(11) 0.2101(3) 0.61225(14) 0.0493(5) Uani 1 1 d . . . C2 C 0.36080(14) 0.2800(4) 0.53605(16) 0.0624(6) Uani 1 1 d . . . H2 H 0.3388 0.4178 0.5338 0.075 Uiso 1 1 calc R . . C3 C 0.35533(16) 0.1410(5) 0.46344(17) 0.0788(8) Uani 1 1 d . . . H3 H 0.3295 0.1864 0.4119 0.095 Uiso 1 1 calc R . . C4 C 0.38728(18) -0.0622(6) 0.4663(2) 0.0881(9) Uani 1 1 d . . . H4 H 0.3838 -0.1534 0.4168 0.106 Uiso 1 1 calc R . . C5 C 0.42464(16) -0.1309(4) 0.54302(18) 0.0729(7) Uani 1 1 d . . . H5 H 0.4460 -0.2695 0.5449 0.087 Uiso 1 1 calc R . . C6 C 0.43091(12) 0.0033(3) 0.61756(15) 0.0526(5) Uani 1 1 d . . . C7 C 0.47195(12) -0.0646(3) 0.70232(16) 0.0568(5) Uani 1 1 d . . . H7 H 0.4663 -0.2213 0.7112 0.068 Uiso 1 1 calc R . . C8 C 0.43540(13) 0.0569(3) 0.78042(14) 0.0516(5) Uani 1 1 d . . . H8A H 0.3808 0.0194 0.7858 0.062 Uiso 1 1 calc R . . H8B H 0.4614 0.0190 0.8361 0.062 Uiso 1 1 calc R . . C9 C 0.44421(10) 0.2971(3) 0.76192(13) 0.0442(4) Uani 1 1 d . . . C10 C 0.57755(12) 0.2026(3) 0.72474(14) 0.0516(5) Uani 1 1 d . . . C11 C 0.55644(11) -0.0049(3) 0.69881(15) 0.0550(5) Uani 1 1 d . . . C12 C 0.61454(17) -0.1460(4) 0.6708(2) 0.0761(7) Uani 1 1 d . . . H12 H 0.6015 -0.2853 0.6520 0.091 Uiso 1 1 calc R . . C13 C 0.69140(17) -0.0819(5) 0.6706(2) 0.0910(9) Uani 1 1 d . . . H13 H 0.7299 -0.1782 0.6521 0.109 Uiso 1 1 calc R . . C14 C 0.71141(14) 0.1237(5) 0.69761(19) 0.0820(8) Uani 1 1 d . . . H14 H 0.7634 0.1661 0.6973 0.098 Uiso 1 1 calc R . . C15 C 0.65488(12) 0.2676(4) 0.72526(16) 0.0634(6) Uani 1 1 d . . . H15 H 0.6684 0.4065 0.7440 0.076 Uiso 1 1 calc R . . C16 C 0.41115(11) 0.4395(3) 0.83538(13) 0.0464(4) Uani 1 1 d . . . C17 C 0.33256(14) 0.4760(4) 0.83894(17) 0.0748(7) Uani 1 1 d . . . H17 H 0.3002 0.4157 0.7955 0.090 Uiso 1 1 calc R . . C18 C 0.30104(17) 0.6013(5) 0.9063(2) 0.0918(9) Uani 1 1 d . . . H18 H 0.2476 0.6242 0.9084 0.110 Uiso 1 1 calc R . . C19 C 0.3480(2) 0.6920(4) 0.96999(18) 0.0838(8) Uani 1 1 d . . . H19 H 0.3266 0.7771 1.0153 0.101 Uiso 1 1 calc R . . C20 C 0.42590(19) 0.6576(4) 0.96693(18) 0.0803(8) Uani 1 1 d . . . H20 H 0.4580 0.7183 1.0105 0.096 Uiso 1 1 calc R . . C21 C 0.45758(14) 0.5330(4) 0.89954(16) 0.0634(6) Uani 1 1 d . . . H21 H 0.5112 0.5120 0.8975 0.076 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0724(9) 0.0486(7) 0.0406(8) 0.0001(6) -0.0038(6) 0.0037(6) O2 0.0469(8) 0.0490(7) 0.0776(10) 0.0010(7) 0.0117(7) -0.0037(6) C1 0.0486(10) 0.0574(11) 0.0418(10) -0.0049(10) 0.0076(8) -0.0138(9) C2 0.0610(14) 0.0766(14) 0.0495(12) 0.0017(12) -0.0030(10) -0.0106(11) C3 0.0717(17) 0.115(2) 0.0501(14) -0.0058(14) -0.0109(11) -0.0231(16) C4 0.096(2) 0.105(2) 0.0633(17) -0.0312(16) 0.0058(14) -0.0328(18) C5 0.0809(17) 0.0678(14) 0.0699(17) -0.0223(13) 0.0127(13) -0.0219(12) C6 0.0536(12) 0.0488(11) 0.0554(12) -0.0057(10) 0.0127(9) -0.0155(8) C7 0.0703(13) 0.0376(9) 0.0624(13) 0.0050(9) 0.0129(11) -0.0039(8) C8 0.0552(12) 0.0511(10) 0.0486(11) 0.0082(9) 0.0046(8) -0.0092(9) C9 0.0431(10) 0.0479(9) 0.0415(10) 0.0031(9) 0.0029(8) -0.0044(7) C10 0.0485(11) 0.0608(12) 0.0455(10) 0.0134(9) 0.0040(8) 0.0072(8) C11 0.0625(12) 0.0521(10) 0.0505(11) 0.0140(9) 0.0062(10) 0.0109(9) C12 0.0795(18) 0.0705(13) 0.0783(17) 0.0087(14) 0.0094(13) 0.0269(12) C13 0.0760(19) 0.108(2) 0.0887(19) 0.0186(18) 0.0139(16) 0.0449(16) C14 0.0504(13) 0.118(2) 0.0779(18) 0.0334(18) 0.0014(12) 0.0179(13) C15 0.0489(12) 0.0821(14) 0.0593(13) 0.0212(12) -0.0012(10) 0.0006(10) C16 0.0481(11) 0.0513(10) 0.0398(10) 0.0031(9) 0.0002(8) -0.0044(8) C17 0.0512(13) 0.1072(17) 0.0660(15) -0.0272(14) 0.0009(11) 0.0012(12) C18 0.0667(17) 0.135(2) 0.0740(18) -0.0255(18) 0.0135(14) 0.0188(16) C19 0.112(2) 0.0880(17) 0.0513(14) -0.0152(13) 0.0174(14) 0.0126(16) C20 0.104(2) 0.0859(17) 0.0513(14) -0.0197(13) -0.0170(13) 0.0049(14) C21 0.0641(13) 0.0702(14) 0.0561(13) -0.0049(11) -0.0137(11) 0.0033(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.378(2) . ? O1 C9 1.426(2) . ? O2 C10 1.376(2) . ? O2 C9 1.427(2) . ? C1 C6 1.385(3) . ? C1 C2 1.386(3) . ? C2 C3 1.383(4) . ? C2 H2 0.9300 . ? C3 C4 1.368(4) . ? C3 H3 0.9300 . ? C4 C5 1.377(5) . ? C4 H4 0.9300 . ? C5 C6 1.389(3) . ? C5 H5 0.9300 . ? C6 C7 1.505(3) . ? C7 C11 1.498(3) . ? C7 C8 1.519(3) . ? C7 H7 0.9800 . ? C8 C9 1.513(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C16 1.513(3) . ? C10 C11 1.384(3) . ? C10 C15 1.388(3) . ? C11 C12 1.388(3) . ? C12 C13 1.378(4) . ? C12 H12 0.9300 . ? C13 C14 1.373(4) . ? C13 H13 0.9300 . ? C14 C15 1.378(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C21 1.372(3) . ? C16 C17 1.370(3) . ? C17 C18 1.377(3) . ? C17 H17 0.9300 . ? C18 C19 1.365(4) . ? C18 H18 0.9300 . ? C19 C20 1.356(4) . ? C19 H19 0.9300 . ? C20 C21 1.376(4) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C9 119.14(14) . . ? C10 O2 C9 120.08(14) . . ? O1 C1 C6 122.65(19) . . ? O1 C1 C2 116.04(18) . . ? C6 C1 C2 121.3(2) . . ? C3 C2 C1 118.7(2) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C4 C3 C2 121.0(2) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 119.7(2) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C5 C6 121.1(3) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C1 118.2(2) . . ? C5 C6 C7 122.8(2) . . ? C1 C6 C7 119.02(18) . . ? C11 C7 C6 110.87(17) . . ? C11 C7 C8 107.83(18) . . ? C6 C7 C8 108.16(16) . . ? C11 C7 H7 110.0 . . ? C6 C7 H7 110.0 . . ? C8 C7 H7 110.0 . . ? C9 C8 C7 107.54(15) . . ? C9 C8 H8A 110.2 . . ? C7 C8 H8A 110.2 . . ? C9 C8 H8B 110.2 . . ? C7 C8 H8B 110.2 . . ? H8A C8 H8B 108.5 . . ? O2 C9 O1 107.65(15) . . ? O2 C9 C16 107.02(14) . . ? O1 C9 C16 106.04(14) . . ? O2 C9 C8 111.24(15) . . ? O1 C9 C8 111.09(15) . . ? C16 C9 C8 113.46(16) . . ? O2 C10 C11 122.60(18) . . ? O2 C10 C15 116.11(19) . . ? C11 C10 C15 121.3(2) . . ? C10 C11 C12 118.3(2) . . ? C10 C11 C7 118.08(18) . . ? C12 C11 C7 123.6(2) . . ? C13 C12 C11 120.7(2) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C14 C13 C12 120.2(2) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 120.3(2) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C15 C10 119.2(2) . . ? C14 C15 H15 120.4 . . ? C10 C15 H15 120.4 . . ? C21 C16 C17 118.5(2) . . ? C21 C16 C9 121.94(19) . . ? C17 C16 C9 119.55(17) . . ? C16 C17 C18 120.5(2) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C19 C18 C17 120.3(3) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C20 C19 C18 119.7(2) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C21 120.2(2) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C16 C21 C20 120.8(2) . . ? C16 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 O1 C1 C6 0.9(3) . . . . ? C9 O1 C1 C2 -179.59(16) . . . . ? O1 C1 C2 C3 178.71(19) . . . . ? C6 C1 C2 C3 -1.8(3) . . . . ? C1 C2 C3 C4 0.2(4) . . . . ? C2 C3 C4 C5 0.8(4) . . . . ? C3 C4 C5 C6 -0.4(4) . . . . ? C4 C5 C6 C1 -1.1(3) . . . . ? C4 C5 C6 C7 -179.4(2) . . . . ? O1 C1 C6 C5 -178.34(19) . . . . ? C2 C1 C6 C5 2.2(3) . . . . ? O1 C1 C6 C7 0.0(3) . . . . ? C2 C1 C6 C7 -179.47(18) . . . . ? C5 C6 C7 C11 90.0(2) . . . . ? C1 C6 C7 C11 -88.2(2) . . . . ? C5 C6 C7 C8 -151.9(2) . . . . ? C1 C6 C7 C8 29.8(2) . . . . ? C11 C7 C8 C9 61.3(2) . . . . ? C6 C7 C8 C9 -58.6(2) . . . . ? C10 O2 C9 O1 -97.06(19) . . . . ? C10 O2 C9 C16 149.31(17) . . . . ? C10 O2 C9 C8 24.9(2) . . . . ? C1 O1 C9 O2 89.74(18) . . . . ? C1 O1 C9 C16 -155.98(14) . . . . ? C1 O1 C9 C8 -32.3(2) . . . . ? C7 C8 C9 O2 -58.5(2) . . . . ? C7 C8 C9 O1 61.5(2) . . . . ? C7 C8 C9 C16 -179.19(17) . . . . ? C9 O2 C10 C11 6.1(3) . . . . ? C9 O2 C10 C15 -173.68(17) . . . . ? O2 C10 C11 C12 178.5(2) . . . . ? C15 C10 C11 C12 -1.7(3) . . . . ? O2 C10 C11 C7 -1.3(3) . . . . ? C15 C10 C11 C7 178.45(19) . . . . ? C6 C7 C11 C10 85.3(2) . . . . ? C8 C7 C11 C10 -32.9(3) . . . . ? C6 C7 C11 C12 -94.6(2) . . . . ? C8 C7 C11 C12 147.2(2) . . . . ? C10 C11 C12 C13 1.2(4) . . . . ? C7 C11 C12 C13 -178.9(2) . . . . ? C11 C12 C13 C14 -0.4(4) . . . . ? C12 C13 C14 C15 0.1(4) . . . . ? C13 C14 C15 C10 -0.5(4) . . . . ? O2 C10 C15 C14 -178.9(2) . . . . ? C11 C10 C15 C14 1.3(3) . . . . ? O2 C9 C16 C21 -23.4(2) . . . . ? O1 C9 C16 C21 -138.06(18) . . . . ? C8 C9 C16 C21 99.7(2) . . . . ? O2 C9 C16 C17 157.11(19) . . . . ? O1 C9 C16 C17 42.4(2) . . . . ? C8 C9 C16 C17 -79.8(2) . . . . ? C21 C16 C17 C18 -0.9(4) . . . . ? C9 C16 C17 C18 178.6(2) . . . . ? C16 C17 C18 C19 0.5(4) . . . . ? C17 C18 C19 C20 -0.3(4) . . . . ? C18 C19 C20 C21 0.5(4) . . . . ? C17 C16 C21 C20 1.1(3) . . . . ? C9 C16 C21 C20 -178.4(2) . . . . ? C19 C20 C21 C16 -0.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.101 _refine_diff_density_min -0.132 _refine_diff_density_rms 0.025 data_cd212526 _database_code_depnum_ccdc_archive 'CCDC 907195' #TrackingRef 'cd212526.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H15 Br O2' _chemical_formula_weight 379.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.9409(6) _cell_length_b 10.8264(12) _cell_length_c 25.900(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1665.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3595 _cell_measurement_theta_min 4.896 _cell_measurement_theta_max 47.203 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.311 _exptl_crystal_size_mid 0.256 _exptl_crystal_size_min 0.147 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 2.477 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.21692 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10066 _diffrn_reflns_av_R_equivalents 0.0818 _diffrn_reflns_av_sigmaI/netI 0.0666 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3275 _reflns_number_gt 2769 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0446P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.010(11) _chemical_absolute_configuration ad _refine_ls_number_reflns 3275 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.0994 _refine_ls_wR_factor_gt 0.0951 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.59992(7) 0.05840(3) -0.002089(13) 0.06326(16) Uani 1 1 d . . . O1 O 1.1351(4) 0.5254(2) 0.15956(8) 0.0464(6) Uani 1 1 d . . . O2 O 1.1547(4) 0.3126(2) 0.15949(8) 0.0439(6) Uani 1 1 d . . . C1 C 0.9815(6) 0.5801(3) 0.12687(11) 0.0405(7) Uani 1 1 d . . . C2 C 1.0461(6) 0.6899(4) 0.10495(12) 0.0521(9) Uani 1 1 d . . . H2 H 1.1852 0.7244 0.1129 0.062 Uiso 1 1 calc R . . C3 C 0.9026(9) 0.7488(3) 0.07100(15) 0.0659(11) Uani 1 1 d . . . H3 H 0.9463 0.8228 0.0558 0.079 Uiso 1 1 calc R . . C4 C 0.6962(8) 0.6991(4) 0.05948(14) 0.0638(11) Uani 1 1 d . . . H4 H 0.5993 0.7398 0.0370 0.077 Uiso 1 1 calc R . . C5 C 0.6335(6) 0.5880(4) 0.08153(12) 0.0532(9) Uani 1 1 d . . . H5 H 0.4953 0.5530 0.0731 0.064 Uiso 1 1 calc R . . C6 C 0.7744(5) 0.5280(3) 0.11620(11) 0.0394(7) Uani 1 1 d . . . C7 C 0.7135(5) 0.4090(3) 0.14223(11) 0.0392(7) Uani 1 1 d . . . H7 H 0.5497 0.4026 0.1457 0.047 Uiso 1 1 calc R . . C8 C 0.8226(5) 0.4096(3) 0.19543(11) 0.0410(8) Uani 1 1 d . . . H8A H 0.7700 0.4798 0.2153 0.049 Uiso 1 1 calc R . . H8B H 0.7845 0.3346 0.2140 0.049 Uiso 1 1 calc R . . C9 C 1.0754(5) 0.4176(3) 0.18748(11) 0.0386(7) Uani 1 1 d . . . C10 C 1.0181(5) 0.2588(3) 0.12334(11) 0.0370(7) Uani 1 1 d . . . C11 C 0.8030(5) 0.2996(3) 0.11240(11) 0.0355(7) Uani 1 1 d . . . C12 C 0.6813(5) 0.2411(3) 0.07424(12) 0.0380(8) Uani 1 1 d . . . H12 H 0.5377 0.2688 0.0659 0.046 Uiso 1 1 calc R . . C13 C 0.7722(6) 0.1418(3) 0.04846(11) 0.0418(8) Uani 1 1 d . . . C14 C 0.9863(6) 0.1005(3) 0.05932(12) 0.0461(8) Uani 1 1 d . . . H14 H 1.0476 0.0345 0.0412 0.055 Uiso 1 1 calc R . . C15 C 1.1081(6) 0.1585(3) 0.09745(11) 0.0427(8) Uani 1 1 d . . . H15 H 1.2513 0.1303 0.1058 0.051 Uiso 1 1 calc R . . C16 C 1.2085(6) 0.4201(3) 0.23712(11) 0.0432(8) Uani 1 1 d . . . C17 C 1.2640(8) 0.5302(4) 0.25986(14) 0.0695(12) Uani 1 1 d . . . H17 H 1.2238 0.6041 0.2441 0.083 Uiso 1 1 calc R . . C18 C 1.3805(10) 0.5318(5) 0.30651(17) 0.0884(16) Uani 1 1 d . . . H18 H 1.4163 0.6068 0.3219 0.106 Uiso 1 1 calc R . . C19 C 1.4418(8) 0.4247(5) 0.32951(14) 0.0755(13) Uani 1 1 d . . . H19 H 1.5207 0.4262 0.3605 0.091 Uiso 1 1 calc R . . C20 C 1.3879(8) 0.3147(5) 0.30713(15) 0.0764(13) Uani 1 1 d . . . H20 H 1.4290 0.2410 0.3230 0.092 Uiso 1 1 calc R . . C21 C 1.2724(7) 0.3128(4) 0.26105(13) 0.0607(11) Uani 1 1 d . . . H21 H 1.2372 0.2374 0.2459 0.073 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0650(2) 0.0652(3) 0.0596(2) -0.0182(2) -0.0188(2) -0.00272(18) O1 0.0369(12) 0.0512(14) 0.0513(12) 0.0111(11) -0.0029(10) -0.0091(12) O2 0.0332(11) 0.0536(14) 0.0448(11) -0.0146(11) -0.0038(9) -0.0001(11) C1 0.0421(17) 0.0408(19) 0.0384(15) -0.0014(15) 0.0051(13) 0.0018(17) C2 0.058(2) 0.049(2) 0.0491(19) -0.0028(17) 0.0047(16) -0.0064(19) C3 0.095(3) 0.048(2) 0.055(2) 0.0071(17) 0.005(2) 0.008(3) C4 0.084(3) 0.056(2) 0.051(2) 0.0020(19) -0.015(2) 0.017(2) C5 0.055(2) 0.057(2) 0.0477(17) -0.0119(17) -0.0096(17) 0.013(2) C6 0.0390(17) 0.0429(18) 0.0362(15) -0.0059(13) 0.0022(13) 0.0070(16) C7 0.0268(14) 0.0475(19) 0.0433(15) -0.0051(14) 0.0025(12) -0.0001(15) C8 0.0358(16) 0.049(2) 0.0381(15) -0.0005(14) 0.0094(13) -0.0017(16) C9 0.0341(16) 0.045(2) 0.0364(14) -0.0014(14) 0.0009(12) -0.0026(16) C10 0.0341(15) 0.043(2) 0.0342(15) 0.0032(14) 0.0000(12) -0.0061(15) C11 0.0304(15) 0.0400(17) 0.0361(16) 0.0027(13) 0.0062(12) -0.0053(15) C12 0.0311(15) 0.0396(19) 0.0432(17) 0.0016(14) -0.0039(12) -0.0039(15) C13 0.0448(19) 0.0403(19) 0.0402(16) -0.0005(14) -0.0070(14) -0.0133(16) C14 0.0498(19) 0.0358(18) 0.0527(18) -0.0022(15) -0.0002(16) -0.0024(17) C15 0.0353(16) 0.0417(19) 0.0512(17) 0.0002(15) -0.0028(15) -0.0017(17) C16 0.0394(17) 0.055(2) 0.0356(15) -0.0018(15) 0.0029(13) -0.0024(18) C17 0.083(3) 0.060(3) 0.066(2) -0.020(2) -0.028(2) 0.025(3) C18 0.107(4) 0.087(3) 0.071(3) -0.039(3) -0.036(3) 0.025(3) C19 0.079(3) 0.105(4) 0.042(2) -0.002(2) -0.0188(19) -0.007(3) C20 0.088(3) 0.083(3) 0.058(2) 0.033(2) -0.022(2) -0.020(3) C21 0.074(3) 0.057(2) 0.051(2) 0.0091(18) -0.0098(19) -0.020(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C13 1.891(3) . ? O1 C1 1.378(4) . ? O1 C9 1.418(4) . ? O2 C10 1.369(4) . ? O2 C9 1.428(4) . ? C1 C2 1.373(5) . ? C1 C6 1.381(5) . ? C2 C3 1.380(5) . ? C2 H2 0.9300 . ? C3 C4 1.372(6) . ? C3 H3 0.9300 . ? C4 C5 1.383(5) . ? C4 H4 0.9300 . ? C5 C6 1.389(4) . ? C5 H5 0.9300 . ? C6 C7 1.499(4) . ? C7 C11 1.510(4) . ? C7 C8 1.523(4) . ? C7 H7 0.9800 . ? C8 C9 1.518(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C16 1.510(4) . ? C10 C11 1.381(4) . ? C10 C15 1.383(4) . ? C11 C12 1.379(4) . ? C12 C13 1.376(4) . ? C12 H12 0.9300 . ? C13 C14 1.377(5) . ? C14 C15 1.376(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.370(5) . ? C16 C21 1.370(5) . ? C17 C18 1.392(6) . ? C17 H17 0.9300 . ? C18 C19 1.353(7) . ? C18 H18 0.9300 . ? C19 C20 1.363(6) . ? C19 H19 0.9300 . ? C20 C21 1.376(5) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C9 120.1(2) . . ? C10 O2 C9 119.4(2) . . ? C2 C1 O1 116.2(3) . . ? C2 C1 C6 121.3(3) . . ? O1 C1 C6 122.5(3) . . ? C1 C2 C3 119.4(4) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 120.6(4) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 119.5(4) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C4 C5 C6 120.7(4) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 118.4(3) . . ? C1 C6 C7 118.4(3) . . ? C5 C6 C7 123.2(3) . . ? C6 C7 C11 111.0(2) . . ? C6 C7 C8 107.5(3) . . ? C11 C7 C8 108.4(3) . . ? C6 C7 H7 109.9 . . ? C11 C7 H7 109.9 . . ? C8 C7 H7 109.9 . . ? C9 C8 C7 107.4(2) . . ? C9 C8 H8A 110.2 . . ? C7 C8 H8A 110.2 . . ? C9 C8 H8B 110.2 . . ? C7 C8 H8B 110.2 . . ? H8A C8 H8B 108.5 . . ? O1 C9 O2 108.3(2) . . ? O1 C9 C16 106.8(3) . . ? O2 C9 C16 105.9(3) . . ? O1 C9 C8 111.3(3) . . ? O2 C9 C8 110.5(3) . . ? C16 C9 C8 113.8(2) . . ? O2 C10 C11 123.5(3) . . ? O2 C10 C15 115.8(3) . . ? C11 C10 C15 120.6(3) . . ? C12 C11 C10 119.0(3) . . ? C12 C11 C7 122.8(3) . . ? C10 C11 C7 118.1(3) . . ? C13 C12 C11 120.1(3) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 121.1(3) . . ? C12 C13 Br1 119.8(2) . . ? C14 C13 Br1 119.1(3) . . ? C15 C14 C13 119.0(3) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C14 C15 C10 120.2(3) . . ? C14 C15 H15 119.9 . . ? C10 C15 H15 119.9 . . ? C17 C16 C21 118.4(3) . . ? C17 C16 C9 120.5(3) . . ? C21 C16 C9 121.0(3) . . ? C16 C17 C18 120.3(4) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C19 C18 C17 120.3(4) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C18 C19 C20 119.9(4) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C19 C20 C21 119.9(4) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C16 C21 C20 121.2(4) . . ? C16 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 O1 C1 C2 174.4(3) . . . . ? C9 O1 C1 C6 -5.9(4) . . . . ? O1 C1 C2 C3 178.7(3) . . . . ? C6 C1 C2 C3 -0.9(5) . . . . ? C1 C2 C3 C4 0.6(6) . . . . ? C2 C3 C4 C5 -1.0(6) . . . . ? C3 C4 C5 C6 1.7(6) . . . . ? C2 C1 C6 C5 1.6(5) . . . . ? O1 C1 C6 C5 -178.1(3) . . . . ? C2 C1 C6 C7 -179.0(3) . . . . ? O1 C1 C6 C7 1.4(4) . . . . ? C4 C5 C6 C1 -2.0(5) . . . . ? C4 C5 C6 C7 178.6(3) . . . . ? C1 C6 C7 C11 -85.7(3) . . . . ? C5 C6 C7 C11 93.8(3) . . . . ? C1 C6 C7 C8 32.8(4) . . . . ? C5 C6 C7 C8 -147.8(3) . . . . ? C6 C7 C8 C9 -61.2(3) . . . . ? C11 C7 C8 C9 58.9(3) . . . . ? C1 O1 C9 O2 96.3(3) . . . . ? C1 O1 C9 C16 -150.0(3) . . . . ? C1 O1 C9 C8 -25.3(4) . . . . ? C10 O2 C9 O1 -89.7(3) . . . . ? C10 O2 C9 C16 156.1(3) . . . . ? C10 O2 C9 C8 32.4(4) . . . . ? C7 C8 C9 O1 58.8(3) . . . . ? C7 C8 C9 O2 -61.5(3) . . . . ? C7 C8 C9 C16 179.5(3) . . . . ? C9 O2 C10 C11 -0.8(4) . . . . ? C9 O2 C10 C15 179.2(3) . . . . ? O2 C10 C11 C12 178.2(3) . . . . ? C15 C10 C11 C12 -1.8(4) . . . . ? O2 C10 C11 C7 -0.4(4) . . . . ? C15 C10 C11 C7 179.6(3) . . . . ? C6 C7 C11 C12 -90.3(3) . . . . ? C8 C7 C11 C12 151.8(3) . . . . ? C6 C7 C11 C10 88.2(3) . . . . ? C8 C7 C11 C10 -29.7(4) . . . . ? C10 C11 C12 C13 1.5(4) . . . . ? C7 C11 C12 C13 -179.9(3) . . . . ? C11 C12 C13 C14 -1.4(5) . . . . ? C11 C12 C13 Br1 177.7(2) . . . . ? C12 C13 C14 C15 1.5(5) . . . . ? Br1 C13 C14 C15 -177.6(2) . . . . ? C13 C14 C15 C10 -1.7(5) . . . . ? O2 C10 C15 C14 -178.1(3) . . . . ? C11 C10 C15 C14 1.9(5) . . . . ? O1 C9 C16 C17 31.4(4) . . . . ? O2 C9 C16 C17 146.7(3) . . . . ? C8 C9 C16 C17 -91.8(4) . . . . ? O1 C9 C16 C21 -150.0(3) . . . . ? O2 C9 C16 C21 -34.7(4) . . . . ? C8 C9 C16 C21 86.8(4) . . . . ? C21 C16 C17 C18 -0.7(6) . . . . ? C9 C16 C17 C18 177.9(4) . . . . ? C16 C17 C18 C19 0.7(8) . . . . ? C17 C18 C19 C20 -0.5(8) . . . . ? C18 C19 C20 C21 0.4(7) . . . . ? C17 C16 C21 C20 0.6(6) . . . . ? C9 C16 C21 C20 -178.0(3) . . . . ? C19 C20 C21 C16 -0.5(7) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.500 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.055